NP-MRD: Showing NP-Card for Tryptoquialanine A (NP0004372)

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Record Information

Version

2.0

Created at

2020-12-09 01:51:19 UTC

Updated at

2021-07-15 16:49:00 UTC

NP-MRD ID

NP0004372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tryptoquialanine A

Provided By

NPAtlas

Description

Tryptoquialanine A is found in Penicillium digitatum. Tryptoquialanine A was first documented in 2002 (PMID: 12381117). Based on a literature review very few articles have been published on (1S)-1-{3-[(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxo-3,4-dihydroquinazolin-2-yl}ethyl acetate (PMID: 33563828) (PMID: 31345413) (PMID: 21591693).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118063D          

 64 69  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118063D          

 64 69  0  0  0  0            999 V2000
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   -0.5558   -0.2648   -1.4553 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6877   -0.8756   -0.8140 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6309    0.2772   -0.8117 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8707    1.4554   -1.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7872   -0.0639   -3.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9077    1.0438   -2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7677    0.8810   -1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.2730   -0.0427 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8533    2.1313    1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6199    3.1155    0.9558 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    1.5840    2.1852 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9370    0.4646    2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445    2.6286    3.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270    1.0267    1.5248 N   0  0  2  0  0  0  0  0  0  0  0  0
    1.4093    0.0643    2.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    0.3429    0.4163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6879    3.9997    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227    3.3056    3.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581    2.6209    2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287    0.4570    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -1.8733    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6059   -1.5088    2.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -0.5537    3.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8665   -2.8242    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8790   -4.2065   -1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7856   -4.4025   -3.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326   -3.2059   -3.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.4279   -2.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -1.2805    0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0611   -1.7410   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674   -0.6983   -3.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468   -0.4515   -4.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7970    0.6976   -4.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    1.5364   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4881    0.8690    3.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057   -0.4162    3.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7017    0.1143    2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566    3.4951    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890    2.1578    4.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7033    2.9699    3.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928    0.4031    3.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860   -0.6537    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 17  7  1  0  0  0  0
 22 18  1  0  0  0  0
 29 24  1  0  0  0  0
 38 30  1  0  0  0  0
 14  9  1  0  0  0  0
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  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  5 42  1  6  0  0  0
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 35 61  1  0  0  0  0
 35 62  1  0  0  0  0
 37 63  1  0  0  0  0
 38 64  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0004372

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]ON1[C@]2([H])N(C(=O)C1(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[C@]21OC(=O)[C@]([H])(N2C(=O)C3=C([H])C([H])=C([H])C([H])=C3N=C2[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H26N4O7/c1-14(37-15(2)32)21-28-18-11-7-5-9-16(18)22(33)29(21)20-13-27(38-23(20)34)17-10-6-8-12-19(17)30-24(27)31(36)26(3,4)25(30)35/h5-12,14,20,24,36H,13H2,1-4H3/t14-,20+,24-,27-/m0/s1

> <INCHI_KEY>
NWBIHDXUFYUNGB-LROXJONJSA-N

> <FORMULA>
C27H26N4O7

> <MOLECULAR_WEIGHT>
518.526

> <EXACT_MASS>
518.180149193

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
53.087899446597476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-1-{3-[(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxo-3,4-dihydroquinazolin-2-yl}ethyl acetate

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.8347730633333335

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.751657049544772

> <JCHEM_PKA_STRONGEST_BASIC>
1.5859506765298659

> <JCHEM_POLAR_SURFACE_AREA>
129.05

> <JCHEM_REFRACTIVITY>
133.18660000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-1-{3-[(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9aH-spiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxoquinazolin-2-yl}ethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 69  0  0  0  0  0  0  0  0999 V2000
   -3.6368    3.0783    2.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169    2.1263    1.9466 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6342   -1.0422    2.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -0.8330    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5948   -1.4902    0.2407 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871   -2.2473   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3730   -2.9093   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9373   -3.6801   -1.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3155   -3.7938   -2.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1273   -3.1214   -2.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5445   -2.3420   -1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722   -1.6763   -2.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320   -1.8116   -3.2316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7716   -0.9079   -1.1307 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5558   -0.2648   -1.4553 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6877   -0.8756   -0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6309    0.2772   -0.8117 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8707    1.4554   -1.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556    1.1711   -1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711    2.0103   -1.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438    0.2572   -1.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6564   -0.2207   -3.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872   -0.0639   -3.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9028    0.5629   -3.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9077    1.0438   -2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7677    0.8810   -1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.2730   -0.0427 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8533    2.1313    1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6199    3.1155    0.9558 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    1.5840    2.1852 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9370    0.4646    2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445    2.6286    3.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270    1.0267    1.5248 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4093    0.0643    2.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    0.3429    0.4163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6879    3.9997    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227    3.3056    3.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581    2.6209    2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6059   -1.5088    2.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -0.5537    3.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8665   -2.8242    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8790   -4.2065   -1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7856   -4.4025   -3.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326   -3.2059   -3.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.4279   -2.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0611   -1.7410   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674   -0.6983   -3.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468   -0.4515   -4.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7970    0.6976   -4.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    1.5364   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4881    0.8690    3.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057   -0.4162    3.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7017    0.1143    2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566    3.4951    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890    2.1578    4.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7033    2.9699    3.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928    0.4031    3.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860   -0.6537    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
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 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
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 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  1
 33 35  1  0
 33 36  1  0
 36 37  1  0
 36 38  1  0
 17  7  1  0
 22 18  1  0
 29 24  1  0
 38 30  1  0
 14  9  1  0
 38 20  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  5 42  1  6
  6 43  1  0
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 18 50  1  6
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 34 57  1  0
 34 58  1  0
 34 59  1  0
 35 60  1  0
 35 61  1  0
 35 62  1  0
 37 63  1  0
 38 64  1  1
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.637   3.078   2.511  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.617   2.126   1.947  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.478   2.621   1.731  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.900   0.815   1.684  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.870  -0.033   1.144  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.634  -1.042   2.289  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.416  -0.833   0.036  0.00  0.00           C+0
HETATM    8  N   UNK     0      -3.595  -1.490   0.241  0.00  0.00           N+0
HETATM    9  C   UNK     0      -4.187  -2.247  -0.693  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.373  -2.909  -0.490  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.937  -3.680  -1.499  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.316  -3.794  -2.724  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.127  -3.121  -2.906  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.545  -2.342  -1.904  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.372  -1.676  -2.078  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.832  -1.812  -3.232  0.00  0.00           O+0
HETATM   17  N   UNK     0      -1.772  -0.908  -1.131  0.00  0.00           N+0
HETATM   18  C   UNK     0      -0.556  -0.265  -1.455  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.688  -0.876  -0.814  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.631   0.277  -0.812  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.871   1.455  -1.006  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.456   1.171  -1.263  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.371   2.010  -1.314  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.644   0.257  -1.898  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.656  -0.221  -3.207  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.787  -0.064  -3.989  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.903   0.563  -3.481  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.908   1.044  -2.181  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.768   0.881  -1.404  0.00  0.00           C+0
HETATM   30  N   UNK     0       3.536   1.273  -0.043  0.00  0.00           N+0
HETATM   31  C   UNK     0       3.853   2.131   1.039  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.620   3.115   0.956  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.093   1.584   2.185  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.937   0.465   2.789  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.744   2.629   3.206  0.00  0.00           C+0
HETATM   36  N   UNK     0       1.927   1.027   1.525  0.00  0.00           N+0
HETATM   37  O   UNK     0       1.409   0.064   2.361  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.492   0.343   0.416  0.00  0.00           C+0
HETATM   39  H   UNK     0      -3.688   4.000   1.910  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.423   3.306   3.576  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.658   2.621   2.480  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.929   0.457   0.987  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.978  -1.873   1.966  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.606  -1.509   2.569  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.146  -0.554   3.155  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.867  -2.824   0.470  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.879  -4.207  -1.339  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.786  -4.402  -3.484  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.633  -3.206  -3.867  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.364  -0.428  -2.564  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.507  -1.281   0.188  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.061  -1.741  -1.421  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.767  -0.698  -3.546  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.747  -0.452  -4.997  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.797   0.698  -4.071  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.775   1.536  -1.773  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.488   0.869   3.647  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.306  -0.416   3.036  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.702   0.114   2.051  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.457   3.495   3.195  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.889   2.158   4.211  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.703   2.970   3.164  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.393   0.403   3.305  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.886  -0.654   0.617  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   42                                             
CONECT    6    5   43   44   45                                             
CONECT    7    5    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   46                                                  
CONECT   11   10   12   47                                                  
CONECT   12   11   13   48                                                  
CONECT   13   12   14   49                                                  
CONECT   14   13   15    9                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18    7                                                  
CONECT   18   17   19   22   50                                             
CONECT   19   18   20   51   52                                             
CONECT   20   19   21   24   38                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   18                                                  
CONECT   23   22                                                            
CONECT   24   20   25   29                                                  
CONECT   25   24   26   53                                                  
CONECT   26   25   27   54                                                  
CONECT   27   26   28   55                                                  
CONECT   28   27   29   56                                                  
CONECT   29   28   30   24                                                  
CONECT   30   29   31   38                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35   36                                             
CONECT   34   33   57   58   59                                             
CONECT   35   33   60   61   62                                             
CONECT   36   33   37   38                                                  
CONECT   37   36   63                                                       
CONECT   38   36   30   20   64                                             
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    6                                                            
CONECT   45    6                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   34                                                            
CONECT   58   34                                                            
CONECT   59   34                                                            
CONECT   60   35                                                            
CONECT   61   35                                                            
CONECT   62   35                                                            
CONECT   63   37                                                            
CONECT   64   38                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  138    0
END

RDKit          3D

64 69  0  0  0  0  0  0  0  0999 V2000
   -3.6368    3.0783    2.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169    2.1263    1.9466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4781    2.6212    1.7308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9001    0.8149    1.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8702   -0.0327    1.1440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6342   -1.0422    2.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -0.8330    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5948   -1.4902    0.2407 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871   -2.2473   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3730   -2.9093   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9373   -3.6801   -1.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3155   -3.7938   -2.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1273   -3.1214   -2.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5445   -2.3420   -1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722   -1.6763   -2.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320   -1.8116   -3.2316 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5558   -0.2648   -1.4553 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6877   -0.8756   -0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6309    0.2772   -0.8117 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8707    1.4554   -1.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556    1.1711   -1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711    2.0103   -1.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438    0.2572   -1.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6564   -0.2207   -3.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872   -0.0639   -3.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9028    0.5629   -3.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9077    1.0438   -2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7677    0.8810   -1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.2730   -0.0427 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8533    2.1313    1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6199    3.1155    0.9558 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    1.5840    2.1852 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9370    0.4646    2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445    2.6286    3.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270    1.0267    1.5248 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4093    0.0643    2.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    0.3429    0.4163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6879    3.9997    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227    3.3056    3.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581    2.6209    2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287    0.4570    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -1.8733    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6059   -1.5088    2.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -0.5537    3.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8665   -2.8242    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8790   -4.2065   -1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7856   -4.4025   -3.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326   -3.2059   -3.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.4279   -2.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -1.2805    0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0611   -1.7410   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674   -0.6983   -3.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468   -0.4515   -4.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7970    0.6976   -4.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    1.5364   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4881    0.8690    3.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057   -0.4162    3.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7017    0.1143    2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566    3.4951    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890    2.1578    4.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7033    2.9699    3.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928    0.4031    3.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860   -0.6537    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 21 22  1  0
 22 23  2  0
 20 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  1
 33 35  1  0
 33 36  1  0
 36 37  1  0
 36 38  1  0
 17  7  1  0
 22 18  1  0
 29 24  1  0
 38 30  1  0
 14  9  1  0
 38 20  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  5 42  1  6
  6 43  1  0
  6 44  1  0
  6 45  1  0
 10 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 18 50  1  6
 19 51  1  0
 19 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 34 57  1  0
 34 58  1  0
 34 59  1  0
 35 60  1  0
 35 61  1  0
 35 62  1  0
 37 63  1  0
 38 64  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1S)-1-{3-[(4'r,9S,9as)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxo-3,4-dihydroquinazolin-2-yl}ethyl acetic acid	Generator
Tryptoquialanine a	MeSH

Chemical Formula

C₂₇H₂₆N₄O₇

Average Mass

518.5260 Da

Monoisotopic Mass

518.18015 Da

IUPAC Name

(1S)-1-{3-[(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxo-3,4-dihydroquinazolin-2-yl}ethyl acetate

Traditional Name

(1S)-1-{3-[(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9aH-spiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxoquinazolin-2-yl}ethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](OC(C)=O)C1=NC2=CC=CC=C2C(=O)N1[C@@H]1C[C@@]2(OC1=O)[C@@H]1N(O)C(C)(C)C(=O)N1C1=CC=CC=C21

InChI Identifier

InChI=1S/C27H26N4O7/c1-14(37-15(2)32)21-28-18-11-7-5-9-16(18)22(33)29(21)20-13-27(38-23(20)34)17-10-6-8-12-19(17)30-24(27)31(36)26(3,4)25(30)35/h5-12,14,20,24,36H,13H2,1-4H3/t14-,20+,24-,27-/m0/s1

InChI Key

NWBIHDXUFYUNGB-LROXJONJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium digitatum	NPAtlas	12381117

Species Where Detected

Species Name	Source	Reference
Penicillium aethiopicum	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.88	ALOGPS
logP	1.83	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	129.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.19 m³·mol⁻¹	ChemAxon
Polarizability	53.09 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA001516

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052423

Chemspider ID

9235524

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11060368

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ariza MR, Larsen TO, Peterson BO, Duus JO, Barrero AF: Penicillium digitatum metabolites on synthetic media and citrus fruits. J Agric Food Chem. 2002 Oct 23;50(22):6361-5. doi: 10.1021/jf020398d. [PubMed:12381117 ]
Costa JH, Bazioli JM, Barbosa LD, Dos Santos Junior PLT, Reis FCG, Klimeck T, Crnkovic CM, Berlinck RGS, Sussulini A, Rodrigues ML, Fill TP: Phytotoxic Tryptoquialanines Produced In Vivo by Penicillium digitatum Are Exported in Extracellular Vesicles. mBio. 2021 Feb 9;12(1). pii: mBio.03393-20. doi: 10.1128/mBio.03393-20. [PubMed:33563828 ]
Costa JH, Bazioli JM, de Vilhena Araujo E, Vendramini PH, de Freitas Porto MC, Eberlin MN, Souza-Neto JA, Fill TP: Monitoring indole alkaloid production by Penicillium digitatum during infection process in citrus by Mass Spectrometry Imaging and molecular networking. Fungal Biol. 2019 Aug;123(8):594-600. doi: 10.1016/j.funbio.2019.03.002. Epub 2019 Mar 22. [PubMed:31345413 ]
Haynes SW, Ames BD, Gao X, Tang Y, Walsh CT: Unraveling terminal C-domain-mediated condensation in fungal biosynthesis of imidazoindolone metabolites. Biochemistry. 2011 Jun 28;50(25):5668-79. doi: 10.1021/bi2004922. Epub 2011 Jun 2. [PubMed:21591693 ]

Showing NP-Card for Tryptoquialanine A (NP0004372)

MOL for NP0004372 (Tryptoquialanine A)

3D MOL for NP0004372 (Tryptoquialanine A)

3D SDF for NP0004372 (Tryptoquialanine A)

3D-SDF for NP0004372 (Tryptoquialanine A)

PDB for NP0004372 (Tryptoquialanine A)

3D PDB for NP0004372 (Tryptoquialanine A)

SMILES for NP0004372 (Tryptoquialanine A)

INCHI for NP0004372 (Tryptoquialanine A)

Structure for NP0004372 (Tryptoquialanine A)

3D Structure for NP0004372 (Tryptoquialanine A)